Sodium Hydroxide → (5-Cyclopropyl-2,4-dimethyl-phenyl)-acetic acid

HRID 1022380Notes

Reaction equation

HRID 1022380 reaction equation
C[O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:10]=[C:9]([CH:11]2[CH2:13][CH2:12]2)[C:8]([CH3:14])=[CH:7][C:6]=1[CH3:15].[OH-].[Na+]>CO>[CH:11]1([C:9]2[C:8]([CH3:14])=[CH:7][C:6]([CH3:15])=[C:5]([CH2:4][C:3]([OH:16])=[O:2])[CH:10]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59614579(5-Cyclopropyl-2,4-dimethyl-phenyl)-acetic acid methyl ester

Product 1

HCID 59614593(5-Cyclopropyl-2,4-dimethyl-phenyl)-acetic acidYield 98.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.5 g of (5-cyclopropyl-2,4-dimethyl-phenyl)-acetic acid methyl ester in 30 ml of methanol is kept at ice bath temperature and treated with 0.5 g of sodium hydroxide in 5 portions. The reaction mixture is stirred at room temperature for 1.5 hours. The solvent is removed in vacuo, the residue poured into water and extracted with diethyl ether. The combined organic phases are dried with sodium sulfate, filtered and concentrated to afford 2.3 g of (5-cyclopropyl-2,4-dimethyl-phenyl)-acetic acid.

Workup

  1. customThe solvent is removed in vacuo
  2. additionthe residue poured into water
  3. extractionextracted with diethyl ether
  4. dry with materialThe combined organic phases are dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3be7e45b54cb4d4f957656702393e31e
Source dataset
uspto-grants-2014_05
Patent number
US08722578B2

Reaction notes

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